(2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one | 768392-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one
• CAS: 768392-05-8
• 化学式: C₃₄H₄₂N₂O₇Si
• 分子量: 618.802
• InChiKey: LUWCYLDZXHOPJB-JBOQNHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以99%的产率得到(S)-4-Benzyl-3-[(1S,2S,3R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-(4-nitro-phenyl)-propyl]-5,5-dimethyl-oxazolidin-2-one
  参考文献：
  名称：

  N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5-dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes

  摘要：

  alpha-Dibenzylamino- and alpha-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the alpha-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding alpha-amino-beta-hydroxy methyl ester or alpha-amino-beta-hydroxyaldehyde proved problematic, with a range of N- and O-protecting groups giving mixtures of products arising from endocyclic and exocyclic cleavage pathways. However, in the et-benzyloxy series, O-silyl protection of the aldol products, and subsequent DIBAL reduction gives stereoselectively the corresponding N-1'-hydroxyalkyloxazolidin-2-ones, which undergo base promoted fragmentation to the desired highly functionalised and differentially protected alpha,beta-dihydroxyaldehydes in good yields and without loss of stereochemical integrity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.123
• 作为产物：
  描述：

  (S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one 在 咪唑 、 4-二甲氨基吡啶 、 三乙基硼 、 三氟甲磺酸 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 (2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5-dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes

  摘要：

  alpha-Dibenzylamino- and alpha-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the alpha-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding alpha-amino-beta-hydroxy methyl ester or alpha-amino-beta-hydroxyaldehyde proved problematic, with a range of N- and O-protecting groups giving mixtures of products arising from endocyclic and exocyclic cleavage pathways. However, in the et-benzyloxy series, O-silyl protection of the aldol products, and subsequent DIBAL reduction gives stereoselectively the corresponding N-1'-hydroxyalkyloxazolidin-2-ones, which undergo base promoted fragmentation to the desired highly functionalised and differentially protected alpha,beta-dihydroxyaldehydes in good yields and without loss of stereochemical integrity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.123